Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Simon A. Herbert; Dominic C. Castell; Jonathan Clayden; Gareth E. Arnott

doi:10.1021/ol4013734

Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Simon A. Herbert, Dominic C. Castell, Jonathan Clayden, Gareth E. Arnott

Research output: Contribution to journal › Article › peer-review

Abstract

The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used. © 2013 American Chemical Society.

Original language	English
Pages (from-to)	3334-3337
Number of pages	3
Journal	Organic Letters
Volume	15
Issue number	13
DOIs	https://doi.org/10.1021/ol4013734
Publication status	Published - 5 Jul 2013

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title = "Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes",

abstract = "The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used. {\textcopyright} 2013 American Chemical Society.",

author = "Herbert, {Simon A.} and Castell, {Dominic C.} and Jonathan Clayden and Arnott, {Gareth E.}",

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AU - Herbert, Simon A.

AU - Castell, Dominic C.

AU - Clayden, Jonathan

AU - Arnott, Gareth E.

PY - 2013/7/5

Y1 - 2013/7/5

N2 - The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used. © 2013 American Chemical Society.

AB - The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used. © 2013 American Chemical Society.

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DO - 10.1021/ol4013734

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JO - Organic Letters

JF - Organic Letters

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ER -

Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Abstract

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